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delta-cadinene

Chemical Structure

General Material Information

Preferred name delta-cadinene
Trivial Name δ-Cadinene
Short Description naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-isopropyl-
Formula C15 H24
CAS Number 483-76-1
FDA UNII 7848KI47OS
Nikkaji Number J2.375.607B
xLogP3-AA 3.80 (est)
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • cadina-1(10),4-diene
  • 1(10),4-cadinadiene
  • (+)-d- cadinene
  • (+)-delta- cadinene
  • d- cadinene
  • 4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene
  • 4,7-dimethyl-1-propan-2-yl-1,2,3,5,6,8a-hexahydronaphthalene
  • naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-
  • naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-isopropyl-
  • Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,8aR)-
  • δ-Cadinene
  • Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)-
  • (1S,8aR)-1,2,3,5,6,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene
  • (+)-δ-Cadinene
  • δ-Cadinene, (+)-
  • (1S-cis)-1,2,3,5,6,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene

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Literature & References

4,7-dimethyl-1-propan-2-yl-1,2,3,5,6,8a-hexahydronaphthalene
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10223
Pubchem (sid):134975172
Flavornet:483-76-1
Pherobase:View
Publications by PubMed
Essential oil characterization of two Azorean Cryptomeria japonica populations and their biological evaluations.
Chemical composition of essential oils from the leaves and stem barks of Vietnamese species of Polyalthia harmandiiPolyalthia jucunda and Polyalthia thorelii.
Chemical composition and major odor-active compounds of essential oil from PINELLIA TUBER (dried rhizome of Pinellia ternata) as crude drug.
Chemical and biological evaluation of Hypericum maculatum Crantz essential oil.
Lavender (Lavandula stoechas L.) essential oils attenuate hyperglycemia and protect against oxidative stress in alloxan-induced diabetic rats.
Juglans regia and J. nigra, two trees important in traditional medicine: A comparison of leaf essential oil compositions and biological activities.
Essential oils composition of croton species from the Amazon.
Analysis of essential oil constituents of three Dasymaschalon species (Annonaceae) from Vietnam.
Chemical composition of the essential oil of Lepidagathis fasciculata from Bondla forest of Goa, India.
Isolation and functional characterization of a τ-cadinol synthase, a new sesquiterpene synthase from Lavandula angustifolia.
Genotoxic effects of Campomanesia xanthocarpa extracts on Allium cepa vegetal system.
A comparative analysis of essential oils of Goniothalamus macrocalyx Ban., Goniothalamus albiflorus Ban. and Goniothalamus tamirensis Pierre ex Fin. & Gagnep. from Vietnam.
Headspace solid-phase microextraction-gas chromatography-mass spectrometry characterization of propolis volatile compounds.
GC and GC-MS analysis of the essential oil of Nepeta cilicica Boiss. ex Benth. from Lebanon.
Antitumour properties of the leaf essential oil of Xylopia frutescens Aubl. (Annonaceae).
Whitening and antioxidant activities of bornyl acetate and nezukol fractionated from Cryptomeria japonica essential oil.
Chemical composition and anti-Trypanosoma cruzi activity of essential oils obtained from leaves of Xylopia frutescens and X. laevigata (Annonaceae).
Phytochemical composition of the essential oil of different populations of Stachys lavandulifolia Vahl.
Essential oils from five species of Annonaceae from Vietnam.
Chemical composition of Hypericum richeri subsp. grisebachii essential oil from Croatia.
Essential oil of flowers of Anaphalis contorta, an aromatic and medicinal plant from India.
Chemical composition and anticancer, antiinflammatory, antioxidant and antimalarial activities of leaves essential oil of Cedrelopsis grevei.
Chemical diversity among the essential oils of wild populations of Stachys lavandulifolia VAHL (Lamiaceae) from Iran.
Chemical composition, antimicrobial and antioxidant properties of the volatile oil and methanol extract of Xenophyllum poposum.
Chemical constituents and anticancer effects of the essential oil from leaves of Xylopia laevigata.
Analysis of chemical constituents and antinociceptive potential of essential oil of Teucrium Stocksianum bioss collected from the North West of Pakistan.
Transcriptome profiling of genes induced by salicylic acid and methyl jasmonate in Polygonum minus.
Bioactive constituents of Homalomena aromatica essential oil and its antifungal activity against dermatophytes and yeasts.
RNAi-mediated Ultra-low gossypol cottonseed trait: performance of transgenic lines under field conditions.
Chemical composition and antimicrobial activity of Salvia x jamensis essential oil.
Determination of genotoxic and antigenotoxic properties of essential oil from Ferula orientalis L. by using Ames/Salmonella and E. coli WP2 bacterial test systems.
Distillation time alters essential oil yield, composition, and antioxidant activity of male Juniperus scopulorum trees.
Study on the volatile oil contents of Annona glabra L., Annona squamosa L., Annona muricata L. and Annona reticulata L., from Vietnam.
Identification and characterization of a kunzeaol synthase from Thapsia garganica: implications for the biosynthesis of the pharmaceutical thapsigargin.
Chemical composition, antibacterial and antifungal activities of essential oil from Cordia verbenacea DC leaves.
Essential oil of Azorella cryptantha collected in two different locations from San Juan Province, Argentina: chemical variability and anti-insect and antimicrobial activities.
Molecular cloning and characterization of (+)-epi-α-bisabolol synthase, catalyzing the first step in the biosynthesis of the natural sweetener, hernandulcin, in Lippia dulcis.
Differences in the volatile compositions of ginseng species (Panax sp.).
Constituents and antimicrobial activity of the essential oils from flower, leaf and stem of Helichrysum armenium.
Chemical composition of the essential oils of Annona pickelii and Annona salzmannii (Annonaceae), and their antitumour and trypanocidal activities.
Comparative Chemical Composition and Antioxidant Properties of the Essential Oils and Aromatic Water from Teucrium persicum Boiss.
Functional characterization of four sesquiterpene synthases from Ricinus communis (castor bean).
A 1,6-ring closure mechanism for (+)-δ-cadinene synthase?
Antifungal properties of Japanese cedar essential oil from waste wood chips made from used sake barrels.
Hemigossypol, a constituent in developing glanded cottonseed (Gossypium hirsutum).
Chemotaxonomy of Serbian Teucrium species inferred from essential oil chemical composition: the case of Teucrium scordium L. ssp. scordioides.
Composition and antimicrobial activity of the leaf and twig oils of Litsea acutivena from Taiwan.
Influence of various growth parameters on fungal growth and volatile metabolite production by indoor molds.
Chemical composition and antimicrobial activity of essential oil of Cupressus atlantica.
Essential oils of Cupressus funebris, Juniperus communis, and J. chinensis (Cupressaceae) as repellents against ticks (Acari: Ixodidae) and mosquitoes (Diptera: Culicidae) and as toxicants against mosquitoes.
Chemical analysis of incense smokes used in Shaxi, Southwest China: a novel methodological approach in ethnobotany.
Ultra-low gossypol cottonseed: generational stability of the seed-specific, RNAi-mediated phenotype and resumption of terpenoid profile following seed germination.
Essential oil composition of the fruits of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae - Periplocoideae).
Chemical composition and antioxidant, antimicrobial, and larvicidal activities of the essential oils of Annona salzmannii and A. pickelii (Annonaceae).
A comparison of headspace solid-phase microextraction and classic hydrodistillation for the identification of volatile constituents from Thapsia spp. provides insights into guaianolide biosynthesis in Apiaceae.
Inter-population variability of terpenoid composition in leaves of Pistacia lentiscus L. from Algeria: a chemoecological approach.
Chemical composition and antimicrobial activity of Anthriscus nemorosa root essential oil.
Chemical composition, antimicrobial and antioxidant activities of essential oil from Gnaphlium affine.
Persistency assessment and aerobic biodegradation of selected cyclic sesquiterpenes present in essential oils.
Chemical composition and phytotoxic effects of essential oils from four Teucrium species.
Genome mining in Streptomyces clavuligerus: expression and biochemical characterization of two new cryptic sesquiterpene synthases.
Composition and antimicrobial activity of the leaf and twig oils of Litsea mushaensis and L. linii from Taiwan.
Free Radical Scavenging Potential and Essential Oil Composition of the Dorema glabrum Fisch. C.A. Mey Roots from Iran.
Antiplasmodial volatile extracts from Cleistopholis patens Engler & Diels and Uvariastrum pierreanum Engl. (Engl. & Diels) (Annonaceae) growing in Cameroon.
Chemical composition and antioxidant and antimicrobial activities of essential oil of Allium sphaerocephalon L. subsp. sphaerocephalon (Liliaceae) inflorescences.
Inhibitor and substrate activities of sesquiterpene olefins toward +-δ-cadinene-8-hydroxylase, a cytochrome P450 monooxygenase (CYP706B1).
Essential oil composition and insecticidal activity of Blumea perrottetiana growing in southwestern Nigeria.
Essential oil composition and variability of Hypericum perforatum from wild populations of northern Turkey.
Biological activity of the essential oil of Kadsura longipedunculata (Schisandraceae) and its major components.
Constituents, antileishmanial activity and toxicity profile of volatile oil from berries of Croton macrostachyus.
Essential oil from leaves of Lippia dulcis grown in Colombia.
Chemical composition and biological properties of Rhododendron anthopogon essential oil.
[Research on liposoluble ingredients of Quchiling].
[Study on the volatile oil of Murraya exotica].
Composition and antimicrobial activity of the leaf essential oil of Litsea nakaii from Taiwan.
Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes.
Crystal structure of (+)-delta-cadinene synthase from Gossypium arboreum and evolutionary divergence of metal binding motifs for catalysis.
Constituents of Cajanus cajan (L.) Millsp., Moringa oleifera Lam., Heliotropium indicum L. and Bidens pilosa L. from Nigeria.
Analysis of essential oil from Teucrium maghrebinum Greuter et Burdet growing wild in Algeria.
Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L.
Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus.
GC-MS analysis and antimicrobial activity of essential oil of Stachys cretica subsp. smyrnaea.
Discrimination of pasture-fed lambs from lambs fed dehydrated alfalfa indoors using different compounds measured in the fat, meat and plasma.
Constituents of leaves and flowers essential oils of Helichrysum pallasii (Spreng.) Ledeb. growing wild in Lebanon.
Essential oil variability in natural populations of Picea omorika, a rare European conifer.
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Detailed analysis of the essential oil from Cistus albidus L. by combination of GC/RI, GC/MS and 13C-NMR spectroscopy.
Isolation of a (+)- delta-cadinene synthase gene CAD1-A and analysis of its expression pattern in seedlings ofGossypium arboreum L.
Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients.
Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia.
Composition, and anti-inflammatory and antioxidant activities of the volatile oil from the fruit peel of Garcinia brasiliensis.
The molecular and biochemical basis for varietal variation in sesquiterpene content in melon (Cucumis melo L.) rinds.
Antimicrobial Activities of Essential Oil and Methanol Extract of Teucrium montanum.
Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting.
Antimicrobial activity of extractable conifer heartwood compounds toward Phytophthora ramorum.
Volatile compounds on the leaf surface of intact and regrowth tarbush (Flourensia cernua DC) canopies.
Anti-inflammation activities of essential oil and its constituents from indigenous cinnamon (Cinnamomum osmophloeum) twigs.
Essential oil composition of Hypericum triquetrifolium Turra. aerial parts.
Variability of the needle essential oils of Pinus heldreichii from different populations in Montenegro and Serbia.
Chemical composition and anti-inflammatory activity of copaiba oils from Copaifera cearensis Huber ex Ducke, Copaifera reticulata Ducke and Copaifera multijuga Hayne--a comparative study.
Compositions and biological activities of essential oils of Kadsura longepedunculata and Schisandra sphenanthera.
A comparison of chemical, antioxidant and antimicrobial studies of cinnamon leaf and bark volatile oils, oleoresins and their constituents.
Chemical composition of the essential oil of Pelargonium quercetorum Agnew. of Iran.
Engineering cottonseed for use in human nutrition by tissue-specific reduction of toxic gossypol.
Constituents of the essential oil from aerial parts of Chromolaena odorata from Thailand.
[Analysis of volatile constituents in leaves of three cypress species by gas chromatography/mass spectrometry].
Changes in terpene content in milk from pasture-fed cows.
Comparative analysis of the oil and supercritical CO(2) extract of Artemisia arborescens L. and Helichrysum splendidum (Thunb.) Less.
Analysis of atmospheric sesquiterpenes: sampling losses and mitigation of ozone interferences.
Engineering cotton (+)-delta-cadinene synthase to an altered function: germacrene D-4-ol synthase.
The pathogen causing Dutch elm disease makes host trees attract insect vectors.
Antisense suppression of a (+)-delta-cadinene synthase gene in cotton prevents the induction of this defense response gene during bacterial blight infection but not its constitutive expression.
Essential Oil of Betula pendula Roth. Buds.
The significance of background odour for an egg parasitoid to detect plants with host eggs.
Chemical composition and antifungal activity of essential oils from different tissues of Japanese Cedar (Cryptomeria japonica).
Analysis of essential oils from wild and micropropagated plants of damiana (Turnera diffusa).
The sesquiterpene hydrocarbons of maize (Zea mays) form five groups with distinct developmental and organ-specific distributions.
Terpenoid aldehyde formation and lysigenous gland storage sites in cotton: variant with mature glands but suppressed levels of terpenoid aldehydes.
Characterization of GaWRKY1, a cotton transcription factor that regulates the sesquiterpene synthase gene (+)-delta-cadinene synthase-A.
Composition and anti-plasmodial activities of essential oils from some Cameroonian medicinal plants.
8-Hydroxy-(+)-delta-cadinene is a precursor to hemigossypol in Gossypium hirsutum.
[Chemical composition of volatile oil from Chromolaena odorata and its effect on plant, fungi and insect growth].
Volatile compounds from leaf-buds of Populus nigra L (Salicaceae).
Reduced levels of cadinane sesquiterpenoids in cotton plants expressing antisense (+)-delta-cadinene synthase.
Characterization of volatiles in Costa Rican guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit.
Volatile compounds emitted by sclerotia of Sclerotinia minor, Sclerotinia sclerotiorum, and Sclerotium rolfsii.
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].
The in vivo synthesis of plant sesquiterpenes by Escherichia coli.
Molecular cloning and functional identification of (+)-delta-cadinene-8-hydroxylase, a cytochrome P450 mono-oxygenase (CYP706B1) of cotton sesquiterpene biosynthesis.
Antibacterial activity of Salvia tomentosa essential oil.
A chemotaxonomic investigation of volatile constituents in Stachys subsect. Swainsonianeae (Labiatae).
Production of yarrow (Achillea millefolium L.) in Norway: essential oil content and quality.
The cyclization of farnesyl diphosphate and nerolidyl diphosphate by a purified recombinant delta-cadinene synthase.
Selective oviposition by Aedes aegypti (Diptera: culicidae) in response to Mesocyclops longisetus (Copepoda: Cyclopoidea) under laboratory and field conditions.
The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria).
Expression pattern of (+)-delta-cadinene synthase genes and biosynthesis of sesquiterpene aldehydes in plants of Gossypium arboreum L.
Flavor compounds of pine sprout tea and pine needle tea.
Expression pattern of genes encoding farnesyl diphosphate synthase and sesquiterpene cyclase in cotton suspension-cultured cells treated with fungal elicitors.
Induction of delta-cadinene synthase and sesquiterpenoid phytoalexins in cotton by Verticillium dahliae.
Coordinated accumulation of (+)-delta-cadinene synthase mRNAs and gossypol in developing seeds of Gossypium hirsutum and a new member of the cad1 family from G. arboreum.
Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase.
Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase.
Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (Mentha x piperita, L.) that produces the aphid alarm pheromone (E)-beta-farnesene.
Composition and antimicrobial activity of the essential oil of Cistus creticus subsp. eriocephalus.
[The constituents of the volatile oil from Achillea wilsoniana].
Cloning and heterologous expression of a second (+)-delta-cadinene synthase from Gossypium arboreum.
Purification of (+)-delta-cadinene synthase, a sesquiterpene cyclase from bacteria-inoculated cotton foliar tissue.
Cloning, expression, and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis.
Volatile Constituents of Origanum dubium Leaves and Stem-Bark.
[Miscellaneous contributions to the essential oils of plants from various territories. LI. On the components of essential oils of Torilis japonica (Houtt.) DC].
Devil's-claw (Proboscidea louisianica), essential oil and its components : Potential allelochemical agents on cotton and wheat.
Volatile Constituents of Uvaria chamae Leaves and Root Bark.
Volatile constituents of Plectranthus rugosus leaf oil.
[Sesquiterpene hydrocarbons from grapes (author's transl)].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C06394
HMDB (The Human Metabolome Database):HMDB35084
FooDB:FDB013710
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 204.35627746582
Boiling Point 120 to 121°C @ 9 mm Hg
Boiling Point 279 to 280°C @ 760 mm Hg
Vapor Pressure 0.007 mmHg @ 25 °C
Flash Point TCC Value 110.56 °C TCC
logP (o/w) 6.271 est
Solubility
alcohol Yes
water, 0.04863 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Herbal
thyme, herbal, woody, dry
General comment At 100.00 %. thyme herbal woody dry

Occurrences

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
natural substances and extractives
Recommendation for delta-cadinene usage levels up to:
not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 30
Click here to view publication 30
average usual ppmaverage maximum ppm
baked goods: 0.900000.90000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: 0.300000.30000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 0.900000.90000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10223
National Institute of Allergy and Infectious Diseases:Data
4,7-dimethyl-1-propan-2-yl-1,2,3,5,6,8a-hexahydronaphthalene
Chemidplus:0000483761